1-Methylimidazole → (3R*,4R*)-3,4-epoxy-6-methoxy-2,2-dimethyl-7-nitro-3,4-dihydro-2H-1-benzopyran

HRID 505640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505640
[CH3:1][O:2][C:3]1[C:4]([N+:15]([O-:17])=[O:16])=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]=[CH:8][C:7]=2[CH:14]=1.CN1C=CN=C1.I(C1C=CC=CC=1)=[O:25].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[O:25]1[C@H:8]2[C@@H:9]1[C:10]([CH3:13])([CH3:12])[O:11][C:6]1[CH:5]=[C:4]([N+:15]([O-:17])=[O:16])[C:3]([O:2][CH3:1])=[CH:14][C:7]=12

Komponenten

6

Edukt 4

HCID 13901-MethylimidazoleHCID 24477Sodium ThiosulfateHCID 92125IodosylbenzeneHCID 591343256-methoxy-2,2-dimethyl-7-nitro-2H-1-benzopyran

Produkt 1

HCID 25196994(3R*,4R*)-3,4-epoxy-6-methoxy-2,2-dimethyl-7-nitro-3,4-dihydro-2H-1-benzopyranAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution (300 mL) of acetonitrile containing 6-methoxy-2,2-dimethyl-7-nitro-2H-1-benzopyran (10.0 g, 42.5 mmol), N-methyl imidazole (0.678 mL, 8.50 mmol), (R,R,S,S)-Ph,Ph salen manganese complex (XY) (880 mg, 0.850 mmol) and iodosobenzene (18.7 mg, 85.0 mmol) were added at room temperature and the mixture was stirred for 2 hours. Upon the completion of the reaction, an aqueous solution of sodium thiosulfate was added to the reaction solution, the resulting solution was filtered through celite. The resulting filtrate extracted with ethyl acetate. The organic phase was washed with water and sodium chloride solution, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=4/1) and the aimed product was obtained as yellow crystals (yield: 75%, optical purity: 99.7% ee).

Aufarbeitung

  1. additionwere added at room temperature
  2. customUpon the completion of the reaction
  3. filtrationthe resulting solution was filtered through celite
  4. extractionThe resulting filtrate extracted with ethyl acetate
  5. washThe organic phase was washed with water and sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter distilling off the solvent
  8. customthe residue was purified by column chromatography (hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-05034daab3d04431af800c571a6403cd
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781483B2

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